Whistles Black One Shoulder Knit Dress
24 Nov 2020

The Ultimate Packing Guide For Winter Sun Or Cosy Staycations

There’s been a lot of uncertainty around travel this year but if you’re lucky enough to be jetting off in the not-too-distant future to catch some winter sun or even take a break closer to home, fashion insider @theindiaedit has got all the tips and tricks you need to pack to perfection. 

The Foundations

  • A good suitcase – One of the markers of adulthood is buying your own suitcase and no longer stealing your parents’. Having a good suitcase really sets you up for organised packing, not to mention making you feel sophisticated and like your life is put together. Our go-to’s are cult favourites AWAY and Horizn Studios – we love having a matching carry-on too for ultimate #suitcasegoals.
  • Bags, bags, bags – We’ve learnt that savvy-packers put all those small bits into bags – we’re talking pants in one, bikinis in another, gadgets in another – you get the gist. This not only makes everything super easy to find, but easy to put away after the trip too. We like reusing the Glossier bubble pouches.
  • Marie Kondo it up – Our latest and greatest hot tip is to roll our clothes Marie Kondo style. This totally transformed our latest trip, making selecting outfits oh-so-easy. Rather than trawling through a messy pile up of items, at a glance we can see it all. We really can’t recommend this enough!
  • Laundry bag – Don’t forget to bring a laundry bag to pop all your dirties into. No one wants their sweaty and sun-creamed clothes contaminating clean pieces. As soon as you get home you can just chuck everything in the wash (except all your rented pieces from Endless Wardrobe – you don’t have to worry about washing those!)


  • Dresses – For us, dresses have to be the most exciting part of packing for a trip. There’s nothing better than popping on a summer dress on holiday and settling down with a spritz in the sun. Or - if country staycation is more your vibe - there’s nothing lovelier than mooching around by the fire in a tiered maxi with a glass of red wine. Not to mention they’re an instant all-in-one outfit so they couldn’t be easier to wear. This trip, why not rent a few to make you feel like you have a whole new wardrobe without the big investment? We love cotton, floaty dresses for days on the beach (like this Free People one), cosy jumper dresses for country walks and Sunday lunches (like this Whistles beauty) and silky showstoppers for evenings out (like these De La Vali + Alexa Chung numbers), because if you can’t dress up on holiday, when can you?!
  • Layers – Layers are a holiday essential – you never know when the breeze could pick up or how much the temperature might drop in the evenings. We’re big fans of a loose linen shirt or kimono (try this reversible Free People one), which will last you year after year and look effortlessly cool over swimwear. Cardigans or a thin black polo are perfect for throwing on over a dress in the evenings too. For colder climes, try a statement cover up like this Whistles panelled leather shirt. Perfect over jeans or open over a midi skirt and polo. 
  • Tops + bottoms – We rely pretty heavily on dresses on holiday, but don’t forget to throw in a few tops + bottoms to mix and match as needed. For a sunny trip we like wide legged trousers, silk slip skirts (like this Essentiel Antwerp A-line midi or the Never Fully Dressed bloom print) and a good pair of shorts (hello Gingham Whistles co-ord). For tops we’ll bring one long-sleeved for cooler nights (this Free People top would be perfect), a versatile cami and then rely on our linen shirts. For a cosy staycation, velvet is the perfect option for a little country pub decadence. Try this Free People number paired with black jeans. Or, we love this Whistles leather A-line mini skirt with a blouse or snuggly knit. 
  • Travelling clothes – For the plane we tend to stick with light layers for comfort and warmth. You want something that will work in cold England and your hot holiday destination. You’ll typically find us in a combination of the above – a cami, wide legged trousers and a linen shirt. If you’re travelling by train or car, try cosy separates like this Whistles merino tube skirt with Converse or white trainers.


  • Handbags – For a week-long trip, you don’t need more than two to three bags. A big straw bag is a must to take you from the airport to days on the beach. If you’re blowing the budget we’re obsessed with the Loewe basket bags or Wood/Grey for more purse-friendly styles. You can throw everything but the kitchen sink in a big one, which suits us perfectly. For evenings and days exploring we like a mini bag or cross-body to fit just the essentials. If you’re on a city break, then a bum-bag is functional and cool. Check out Azurina for stylish, affordable and customisable styles.
  • Hats – We can’t get enough of straw hats for sunny breaks – not only do they look uber chic, but they provide great sun protection. Our absolute favourites are from Lack Of Color. We recommend wearing/carrying yours as you travel so they don’t get misshapen. If you’re staying closer to home, a camel beret or borg bucket hat will look super cute with that snuggly coat.


  • Chunky sandals – Birkenstocks are the perfect chunky, comfy sandal that seem to go with everything and last forever. You’ll wear them at home and away. If you’re looking for a more elevated chunky sandal then Isabel Marant is your gal (or Prada if you’re really looking to invest).
  • Biker boots - A weekend in the country isn’t complete without a chunky boot. Go for a platform biker style to toughen up floral midi dresses (AllSaints do amazing stompers) or embrace a hiking boot spin for added outdoorsy points.
  • Trainers – perfect for travelling, hiking, city strolls and making outfits more casual.


  • Workout equipment – We love a quick workout on holiday, just so we don’t feel like we’ve completely lost it when we get home. A blow-up Pilates ball and some bands are perfect to travel with and then you can just find workouts on YouTube.
  • Steamer – We can’t live without a travel steamer, especially when bringing beautiful dresses along.
  • Camera – You’ve got to capture all those Endless Wardrobe outfits somehow…

We hope you loved our packing guide with @theindiaedit – if you are lucky enough to be heading off for a break, tag us in your holiday snaps @endlesswardrobe #endlessmoments

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